Diisopropylethylamine → HCID 58981734, compound

Participants

Reaction Steps

To a solution of 100 mg (0.41 mmol) of tert-butyl (1S)-1-[(1S)-2-amino-1-hydroxyethyl]pentylcarbamate & tert-butyl (1S)-1-[(1R)-2-amino-1-hydroxyethyl]pentylcarbamate and 0.070 mL (0.41 mmol) of N,N-diisopropylethylamine in 2 mL dichloromethane was added 0.050 mL (0.41 mmol) 4-morpholinecarbonyl chloride. The reaction mixture was stirred at room temperature for 18 h, diluted with dichloromethane, and washed with 1N hydrochloric acid and brine. After drying over anhydrous magnesium sulfate, the solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography eluting with ethyl acetate to afford 130 mg (89%) of tert-butyl (1S)-1-{(1S)-1-hydroxy-2-[(4-morpholinylcarbonyl)amino]ethyl}pentylcarbamate & tert-butyl (1S)-1-{(1R)-1-hydroxy-2-[(4-morpholinylcarbonyl)amino]ethyl}pentylcarbamate. 1H-NMR (300 MHz, DMSO-d6): δ 6.55–6.36 (m, 2H), 5.00–4.65 (m, 1H), 3.60-3.23 (m, 9H), 3.10–2.80 (m, 2H), 1.40–1.05 (m, 15 H), 0.87 (m, 1H); ES-LCMS m/z 382 (M+Na).

Provenance & Evidence